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http://dx.doi.org/10.5012/bkcs.2012.33.5.1556

A Simple and Efficient One-Pot Three-Component Synthesis of Propargylamines Using Bismuth (III) Chloride  

Teimouri, Abbas (Department of Chemistry, Payame Noor University (PNU))
Chermahini, Alireza Najafi (Department of Chemistry, Isfahan University of Technology)
Narimani, M. (Department of Chemistry, Payame Noor University (PNU))
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.5, 2012 , pp. 1556-1560 More about this Journal
Abstract
A simple highly versatile and efficient method has been developed for the three-component coupling of aldehydes, amines and alkynes to prepare propargylamines, in the presence of a catalytic amount of $BiCl_3$. The advantages of methods are high yield, mild reaction conditions, no environmental pollution and easy work up procedure.
Keywords
Bismuth (III) chloride; Green synthesis; Propargylamines; Three component reaction;
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1 Colombo, F.; Benaglia, M.; Orlandi, S.; Usuelli, F. J. Mol. Catal. A: Chem. 2006, 260, 128.   DOI
2 Gommermann, N.; Knochel, P. Chem. Eur. J. 2006, 12, 4380.   DOI   ScienceOn
3 Bisai, A.; Singh, V. K. Org. Lett. 2006, 8, 2405.   DOI   ScienceOn
4 Li, C.-J.; Wei, C. Chem. Commun. 2002, 268.
5 Park, S. B.; Alper, H. Chem. Commun. 2005, 1315.
6 Black, D. A.; Arndtsen, B. A. Tetrahedron 2005, 61, 11317.   DOI   ScienceOn
7 Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143.   DOI   ScienceOn
8 Gommermann, N.; Knochel, P. Chem. Commun. 2004, 2324.
9 Gommermann, N.; Knochel, P. Synlett 2005, 2799.
10 Colombo, F.; Benaglia, M.; Orlandi, S.; Usuelli, F.; Celentano, G. J. Org. Chem. 2006, 71, 2064.   DOI   ScienceOn
11 Dyker, G. Handbook of C-H Transformations; Wiley-VCH: Weinheim, 2005
12 Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.   DOI
13 Wei, C.; Li, Z.; Li, C. J. Org. Lett. 2003, 5, 4473.   DOI   ScienceOn
14 Wei, C.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584.   DOI   ScienceOn
15 Matyus, P.; Dajka-Halasz, B.; Foldi, A.; Haider, N.; Barlocco, D.; Magyar, K. Curr. Med. Chem. 2004, 11, 1285.   DOI   ScienceOn
16 Li, P.; Wang, L. Tetrahedron 2007, 63, 5455.   DOI   ScienceOn
17 Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.   DOI   ScienceOn
18 Naota, I.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599.   DOI   ScienceOn
19 Zimmermann, K.; Waldmeier, P. C.; Tatton, W. G. Pure Appl. Chem. 1999, 71, 2039.   DOI   ScienceOn
20 Boulton, A. A.; Davis, B. A.; Durden, D. A.; Dyck, L. E.; Juorio, A. V.; Li, X. M.; Paterson, I. A.; Yu, P. H. Drug Dev. Res. 1997, 42, 150.   DOI   ScienceOn
21 Teimouri, A.; Najafi Chermahini, A. Arabian Journal of Chemistry, In Press, Corrected Proof, Available online 2 June 2011.
22 Dabbagh, H. A.; Teimouri, A.; Najafi Chermahini, A.; Shiasi, R. Spectrochimica Acta Part A 2007, 67, 437.   DOI   ScienceOn
23 Dabbagh, H. A.; Teimouri, A.; Najafi Chermahini, A. Applied Catalysis B: Environmental. 2007, 76, 24.   DOI   ScienceOn
24 Bhatte, K. D.; Sawant, D. N.; Deshmukh, K. M. Bhanage, B. M. Catal. Commun. 2011, 16, 114.   DOI   ScienceOn
25 Rahman, M.; Bagdi, A. Kr.; Majee, A.; Hajra, A. Tetrahedron Lett. 2011, 52, 4437.   DOI   ScienceOn
26 Du, W. Q.; Zhang, J. M.; Wu, R.; Liang, Q.; Zhu, S. Z. J. Fluorine Chem. 2008, 129, 695.   DOI   ScienceOn
27 Sreedhar, B.; Suresh Kumar, A.; Reddy, P. S. Tetrahedron Lett. 2010, 51, 1891.   DOI   ScienceOn
28 Sreedhar, B.; Reddy, P. S.; Prakash, B. V.; Ravindra, A. Tetrahedron Lett. 2005, 46, 7019.   DOI   ScienceOn
29 Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Divers. 2003, 7, 135.   DOI
30 Alakesh, B.; Vinod, K. S. Org. Lett. 2006, 8, 2405.   DOI   ScienceOn
31 Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.   DOI   ScienceOn
32 Matano, Y.; Ikegami, T. In Organobismuth Chemistry; Suzuki, H., Manato, Y., Eds.; Elsevier: New York, 2001; Chapter 2; pp 21-245.
33 De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2004, 45, 7407.   DOI   ScienceOn
34 Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249.
35 Soleimani, E.; Khodaei, M. M.; Koshvandi, A. T. K. Chinese Chem. Lett. 2011, 22, 927.   DOI   ScienceOn
36 Li, H.; Zeng, H.; Shao, H. Tetrahedron Lett. 2009, 50, 6858.   DOI   ScienceOn
37 De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 8345.   DOI   ScienceOn
38 Sabitha, G.; Reddy, E. V.; Maruthi, C.; Yadav J. S. Tetrahedron Lett. 2002, 43, 1573.   DOI   ScienceOn
39 Sabitha, G.; Reddy, E. V.; Yadav, J. S.; Krishna, K. V. S.; Sankar, R. Tetrahedron Lett. 2002, 43, 4029.   DOI   ScienceOn
40 Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C. J. Tetrahedron Lett. 2004, 45, 2443.   DOI   ScienceOn
41 Teimouri, A.; Najafi Chermahini, A. Journal of Molecular Catalysis A: Chemical 2011, 346, 39.   DOI   ScienceOn
42 Yan, W.; Wang, R.; Xu, Z.; Xu, J.; Lin, L.; Shen, Z.; Zhou, Y. J. Mol. Catal. A: Chem. 2006, 255, 81.   DOI   ScienceOn
43 Reddy, K. M.; Babu, N. S.; Prasad, P. S. S.; Lingaiah, N. Tetrahedron Lett. 2006, 47, 7563.   DOI   ScienceOn
44 Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358.   DOI   ScienceOn
45 Li, P.; Wang, L.; Zhang, Y.; Wang, M. Tetrahedron Lett. 2008, 49, 6650.   DOI   ScienceOn
46 Wang, S.; He, X.; Song, L.; Wang, Z. Synlett 2009, 447.
47 Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Sreedhar, B. Tetrahedron Lett. 2004, 45, 7319.   DOI   ScienceOn
48 Wang, M.; Li, P.; Wang, L. Eur. J. Org. Chem. 2008, 2255.
49 Bisai, A.; Singh, V. K. Tetrahedron 2011, In Press
50 Sreedhar, B.; Reddy, P. S.; Krishna, C. S. V.; Babu, P. V. Tetrahedron Lett. 2007, 48, 7882.   DOI   ScienceOn
51 Likhar, P. R.; Roy, S.; Roy, M.; Subhas, M. S.; Kantam, M. L.; De, R. L. Synlett 2007, 2301.
52 Namitharan, K.; Pitchumani, K. Eur. J. Org. Chem. 2010, 411.
53 Maggi, R.; Bello, A.; Oro, C.; Sartori, G.; Soldi, L. Tetrahedron 2008, 64, 1435.   DOI   ScienceOn
54 Patil, M. K.; Keller, M.; Reddy, B. M.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2008, 4440.
55 Kantam, M. L.; Balasubrahmanyam, V.; Kumar, K. B. S.; Venkanna, G. T. Tetrahedron Lett. 2007, 48, 7332.   DOI   ScienceOn
56 Mukhopadhyay, C.; Rana, S. Catal. Commun. 2009, 11, 285.   DOI   ScienceOn
57 Kantam, M. L.; Yadav, J.; Laha, S.; Jha, S. Synlett 2009, 1791.
58 Aliaga, M. J.; Ramon, D. J.; Yus, M. Org. Biomol. Chem. 2010, 8, 43.   DOI   ScienceOn
59 Kidwai, M.; Bansal, V.; Mishra, N. K.; Kumar, A.; Mozumdar, S. Synlett 2007, 1581.
60 Kantam, M. L.; Laha, S.; Yadav, J.; Bhargava, S. Tetrahedron Lett. 2008, 49, 3083.   DOI   ScienceOn
61 Ramu, E.; Varala, R.; Sreelatha, N.; Adapa, S. R. Tetrahedron Lett. 2007, 48, 7184.   DOI   ScienceOn
62 Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.   DOI   ScienceOn
63 Pinet, S.; Pandya, S. U.; Chavant, P. Y.; Ayling, A.; Vallee, Y. Org. Lett. 2002, 4, 1463.   DOI   ScienceOn
64 Zani, L.; Alesi, S.; Cozzi, P. G.; Bolm, C. J. Org. Chem. 2006, 71, 1558.   DOI   ScienceOn
65 Lee, K.-Y.; Lee, C.-G.; Na, J.-E.; Kim, J.-N. Tetrahedron Lett. 2005, 46, 69.   DOI   ScienceOn
66 Jiang, B.; Si, Y.-G. Tetrahedron Lett. 2003, 44, 6767.   DOI   ScienceOn
67 Fischer, C.; Carreira, E. M. Org. Lett. 2004, 6, 1497.   DOI   ScienceOn
68 Jiang, B.; Si, Y.-G. Angew. Chem., Int. Ed. 2004, 43, 216.   DOI   ScienceOn
69 Chen, W. W.; Nauyen, R. V.; Li, C. J. Tetrahedron Lett. 2009, 50, 2895.   DOI   ScienceOn
70 Jadav, J. S.; Reddy, B. V. S.; Gopal, A. V. H.; Patil, K. S. Tetrahedron Lett. 2009, 50, 3993.
71 Zhang, Y.; Li, P.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364.   DOI   ScienceOn
72 Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.   DOI   ScienceOn
73 Sakaguchi, S.; Kubo, T.; Ishii, Y. Angew. Chem., Int. Ed. 2001, 40, 2534.   DOI   ScienceOn
74 Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273.   DOI   ScienceOn
75 Sakaguchi, S.; Mizuta, T.; Furuwan, M.; Kubo, T.; Ishii, Y. Chem. Commun. 2004, 1638.
76 Hua, L. P.; Lei, W. Chin. J. Chem. 2005, 23, 1076.   DOI   ScienceOn
77 Samai, S.; Nandi, G. C.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5555.   DOI   ScienceOn
78 Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244.   DOI   ScienceOn
79 Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Lett. 2006, 35, 1376.   DOI   ScienceOn
80 Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659.   DOI   ScienceOn
81 Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.   DOI   ScienceOn
82 Lo, V. K. Y.; Liu, Y.; Wong, M. K.; Che, C. M. Org. Lett. 2006, 8, 1529.   DOI   ScienceOn
83 Ji, J.-X.; Au-Yeung, T. T. L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42.   DOI   ScienceOn
84 Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A. Org. Lett. 2004, 6, 1001.   DOI   ScienceOn
85 Huma, H. Z. S.; Halder, R.; Karla, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485.   DOI   ScienceOn
86 Kabalka, G. W.; Wang, L.; Pagni, R. M. Synlett 2001, 676.
87 Wei, C.; Li, C.- J. J. Am. Chem. Soc. 2002, 124, 5638.   DOI   ScienceOn
88 Wei, C.; Mague, J. T.; Li, C. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749.   DOI   ScienceOn
89 Gommarman, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.   DOI   ScienceOn